Emulsification agents



United States Patent 3,244,534 EMUESIFICATION AGENTS Bruce D. Buddemeyer, Overland Park, Kans., John Robert Moneymaker, Kansas City, Mo., and Maurice Charles Meyer, Kansas City, Kans., assignors to The Paniplus Company, Kansas City, Mo., a corporation of Missouri N0 Drawing. Filed Dec. 28, 1961, Ser. No. 162,946

14 Claims. (Cl. 99-91) This application is a continuation-in-part of our copending application Serial No. 162,927 filed December 28, 1961 now U.S.P. 3,141,030.

This invention is concerned with improved emulsification agents which are especially useful in food products, cosmetics and pharmaceutical preparations.

The addition agents of the present invention are of a lipoidal nature and when added as ingredients in, for instance, bakery products, considerably improve their physical properties resulting in enhanced consumer appeal. The addition agents may be employed as separate ingredients, or may be admixed with other ingredients of the formulae and in this form incorporated into the formulation from which the products are made.

An object of the present invention is to provide new and improved agents of a lipoidal character, which, when added as ingredients to baked leavened dough products, considerably improve the properties of such products.

Another object of the present invention is the provision of shortening compositions containing such addition agents.

Another object of the present invention is to provide new and improved agents which, when included as ingredients in icings, fillings, fondants, creams and the like, considerably improve their properties and usefulness.

Other objects of the present invention will in part be obvious and will in part be made clear from the following description.

The agents of the present invention comprise, in combination: (1) acyl lactylic acids, including salts thereof; and (2) certain polyol esters of fatty acids.

The polyol esters of fatty acids may be characterized as mono-and/or di-fatty acid esters of aliph'atid polyhydric alcohols or derivatives thereof.

The acyl lactylic acids and their corresponding salts forming part of the addition agents disclosed herein correspond to the formula wherein RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtures thereof, Z is a cation and n is a number which represents the average number of lactyl, i.e., (OCHCH CO), groups present per molecule. The value of n may vary from about 0.1 to 10.0 and is preferably between about 0.3 and 6.0. Best results are achieved with acyl lactylic acid compositions having a value for n of greater than zero and less than 1, or between about 0.3 and 0.9, and such materials are preferred for use.

The cation Z in the above formula may be selected from the group consisting of hydrogen, when the material is in the acid form, and alkali metals, when the material is in the salt form. Among the preferred alkali metal cations may be mentioned sodium and potassium.

The acyl lactylates are prepared by reaction of fatty acids of the type described or derivatives thereof and lactic acid or its derivatives.

The method of making acyl lactylic acid compounds with n values greater than 1 is well understood in the art, suitable methods being disclosed, for example, in United States Patents Nos. 2,793,270 and 2,733,252.

See

The acyl lactylic acid compositions with n values less than 1 are recent in origin, and they, together with their method of preparation, are disclosed in our co-pending application, Serial No. 162,927 filed December 28, 1961, now Patent No. 3,141,030.

The monoand/or di-fatty acid esters of aliphatic polyhydric alcohols, or derivatives thereof, forming part of the addition agents disclosed herein may be characterized, in whole or in part, as the reaction products of fatty acyl compounds containing 16 to 24 carbon atoms, or mixtures thereof, with aliphatic polyhydric alcohols or derivatives thereof, containing at least 2 or 'between about 2 and 10 hydroxyl groups in the aliphatic chain. Preferably the number of carbon atoms in the aliphatic chain of the polyhydric alcohols is fewer than about 12.

As examples of the polyhydric alcohols may be mentioned the dihydric alcohols, such as ethylene glycol, propylene glycol, butylene glycol, and the like; the trihydric alcohols, such as glycerol; and the higher aliphatic polyhydric alcohols, such as sorbitol.

As examples of the monoand di-fatty acid esters of aliphatic polyhydric alcohols forming part of the addition agents disclosed herein, and preferred for use, may be mentioned the mono-fatty acid esters of glycerol, more commonly referred to as mono-glycerides, including compositions comprising mixtures of monoand di-glycerides; propylene glycol monostearate; glyceryl lactopalmitate; glyceryl lactostearate; sorbitan monostearate; and polyoxyethylene (n) sorbitan monostearate; including mixtures of the foregoing.

The mono-glycerides, or mixtures of monoand diglycerides are prepared by procedures which are now well known, as for example, by careful alcoholysis of naturally occurring fats with glycerol.

Sorbitan monostearate is a mixed partial stearic ester of sorbitol anhydride. Polyoxyethylene (n) sorbitan monostearate is a complex mixture of polyoxyethylene ethers of mixed partial stearic esters of sorbitol anhydride. The (n) refers to the average number of polyoxyethylene groups present per mole of the composition, and may range from 1 to or more, although usually it will range between about 10 and 30. Particularly suitable for use is olyoxyethylene (20) sorbitan monostearate, which contains about 20 polyoxyethylene groups per mole of the composition.

Propylene glycol monostearate may be made by the reaction of propylene glycol and stearic acid.

Glyceryl lactopalmitate is the name given to the product obtained by the reaction of glycerol, higher fatty acids comprising at least about 50 percent by weight palmitic acid, and lactic acid. The method of making glyceryl lactopalmitate is well known, and a particularly advantageous method is described in United States Patent No. 2,690,971.

Glyceryl lactostearate is a product obtained by a similar reaction as stated above with the exception that stearic acid is substituted for palmitic acid.

As described in the referred to patent, glyceryl lactopalmitate may be prepared by reacting glycerol with about 1 equivalent mol per mol of glycerol of a mixture of myristic, palmitic and stearic acids containing at least 50 percent by weight palmitic acid, and between about 0.5 and 1 mol of lactic acid per mol of glycerol.

In carrying out the reaction, the mixed fatty acids, glycerol and lactic acid are heated to a temperature of about C., in a vacuum with removal of water formed by the reaction; refluxing of lactic acid; and sparging with an inert gas, such as CO and maintained at such conditions until the acid number of the reaction product is below about 8.1. The reaction product is then washed with water until substantially free of water-soluble material. The water washed reaction product comprises about 40-50 percent of mixed lactic acid-fatty acid diglycerides; about 16-25 percent monoglycerides; and the balance substantially all diglycerides of the fatty acids. The amount of triglycerides in the reaction product is quite low, and is usually less than about 1 percent.

The following are typical formulae for the addition agents disclosed herein:

EXAMPLE 1 Ingredients: Weight percent Acyl lactylates to 90 Monoglycerides of fatty acids 90 to 10 EXAMPLE 2 Ingredients: Weight percent Acyl lactylates 10 to 90 Mixture of monoand di-glycerides of fatty acids 90 to 10 EXAMPLE 3 Ingredients: Weight percent Acyl lactylates 1 to 99 Mixture of the following:

5 to wt. percent polyoxyethylene 20 sorbitan monostearate; 80 to 95 wt. percent sorbitan monostearate 99 to 1 EXAMPLE 4 Ingredients: Weight percent Acyl lactylates 10 to 90 Propylene glycol monostearate 90 to 10 EXAMPLE 5 Ingredients: Weight percent Acyl lactylates 10 to 90 Glyceryl lactopalmitate 90 to 10 In the addition agents, the weight ratio of the monoand/ or di-ester to the acyl lactylate may vary from about 0.01 to 100, and is usually between about 0.1 and 100. Preferably, and for best results, this weight ratio is between about 0.33 and 10.

As already described, the addition agents disclosed herein may be added as an ingredient to bakery goods either separately, or admixed with conventional ingredients.

Preferably, the addition agents are mixed with the shortening or water, and in this way introduced into the formulae for making the baked goods.

Regardless of whether the addition agents are incorporated as such or in admixture with other ingredients, the amount of the addition agent added to the bakery products may comprise between about 0.1 and percent by weight, based upon the shortening weight, and is preferably between about 0.3 and 10 percent, based upon the shortening weight.

Shortenings with which the addition agents of the present invention may be combined are of the usual type, and in general are triglyceride oils or fats derived from animal sources such as lard or tallow and from plant sources such as the seed oils or corn, cotton, soy and the like. It is normal practice for those shortenings to be refined and processed to improve their properties. The usual treatments include catalytic hydrogenation to improve the plasticity, increase hardness and reduce the iodine number of the fatty material, and heat treatment in the presence of alkaline catalysts, with or without added glycerine, to improve the physical properties and functionality. For instance, the plastic super-glycerinated vegetable shortenings have been hydrogenated and subjected to inter-esterification reactions to improve the physical characteristics and increase the content of monoand diglycerides and to increase the emulsification properties of the shortening. Shortenings of the usual type may also contain glycerine and/or natural or hydroxylated lecithin.

When the addition agents are to be combined with sohrtening and/ or oil, this may be done by dissolving the agents in the usual type shortening, and then stirring and tempering the resulting mixture. Final treatment may also include the chilling and whipping treatments of the Votator process in the case of plastic shortenings.

As indicated above, the amount of the addition agent in the baked leavened dough products may comprise between about 0.1 and 30 percent, based upon the weight of the shortening. Shortening compositions containing the desired amount of addition agent may be prepared and added in lieu of the usual shortening. Obviously, however, mixtures of the usual shortenings and larger amounts of the addition agent can be produced, and this admixture can be used in lieu of only a portion of the usual shortening with the same net benefits resulting, and such compositions are to be considered part of this invention. Thus, shortenings containing anywhere from 0.1 to 99 weight percent or more of the addition agents disclosed herein are within the purview of the instant invention.

The ingredients employed in making baked leavened products form no part of the present invention since any suitable formula may be used. The basic ingredients used in the manufacture of bread, for example, are flour, water, sodium chloride and yeast. For commercial bread, sugar, milk and shortening are conventionally added to these basic ingredients. For cake, or other sweet leavened products, eggs as well as other enriching agents may be added. Ordinarily, in making cake, chemical leavening agents, such as baking powder, rather than yeast, are employed.

The addition agents disclosed herein are especially suitable for use in cake formulae, and when added to such formulae provide for improved batter aeration and stability, symmetry and grain characteristics. The cakes obtained by using these addition agents are desirably tender or short and have superior eating and keeping qualities. In addition, the use of the addition agents disclosed herein makes it much easier to prepare a satisfactorily balanced formula for a high ratio prepared dry cake mix. By a high ratio prepared dry cake mix is meant one with a high ratio of sugar to flour. The sweeter or higher this ratio (over 1:1) in cakes, the better will be the properties and keeping qualities of the confection.

The cake mixes according to the invention can be prepared, for example, by thoroughly blending together the usual mix ingredients, such as flour, baking powder and sugar, with the addition agents disclosed herein. Preferably, the addition agents are added to the shortening, or to Water to form a water dispersion, and in either of these forms are blended with the dry ingredients of such a mix before addition of the ordinary liquid ingredients, such as water, milk, eggs, fiavorings and the like.

The following examples will serve to illustrate the preparation of cake incorporating the addition agents disclosed herein.

To demonstrate in part the effect of the additives of the present invention, the monoand/ or di-fatty acid esters of aliphatic polyhydric alcohols or derivatives thereof, forming one part of the two part addition agents disclosed herein, were bake tested to establish optimum functionality of such materials alone in a typical commercial white cake formula and procedure. For comparison, representative two part additives disclosed herein were tested using identical procedures.

EXAMPLE 6 Two parts by Weight commercial vegetable shortening comprising essentially triglycerides were melted with one one part of a commercially distilled glyceryl monostearate, which will be referred to as the one-part'emulsifie'r.

The homogeneous molten mixture was whipped with a small propellant type mixer and rapidly chilled until a soft plastic mixture was obtained.

This preparation was compared in baking tests with a representative mixture of the two part additives disclosed herein and composed of two parts by weight shortening and one-half part of distilled glyceryl monostearate and one-half part of a stearyl lactylic acid which contained an average of 0. 9 lactyl groups per molecule. This physically similar material will be referred to as the combination emulsifier.

The following recipe and procedure was employed to establish the eifects of various levels of distilled monoglycerides:

The emulsifier was included as a partial substitute for shortening, so that the total base oil and emulsifier equaled 36 percent based on the flour weight.

Shortening and emulsifier were added to the total dry mix (869.3 grns.), cut in, and mixed for four minutes on first speed (slow) using a Hobart C-100 mixer equipped with a three quart bowl and batter paddle.

First stage.--Over a one-minute period 225 mls. of water was added while mixing at first speed, the bowl was scraped and mixing continued at first speed two minutes.

Second stage.-All of the eggs were added over a oneminute period at first speed, the bowl scraped down, and mixing continued two and one-half minutes at second speed.

Third stage.Over a one-minute period 102 mls. of water was added while mixing at first speed, the bowl scraped down, and mixing continued three minutes at first speed.

The temperature of the water and eggs was controlled so that batter temperature was controlled between 72 F. and 75 F.

368 gms. of batter was scaled into two 8 inch diameter by 1 /2 inch cake pans and baked at 375 F. for twentyfour minutes. Cakes were allowed to cool for forty-five minutes prior to measuring volume by rape seed displacement and cut for quality comparisons.

Cake quality was evaluated with the system used by the American Institute of Baking and is a summary of the following factors:

The term Bake refers to the overall general external appearance of the uniced cake.

In these evaluations, the factor of icing and filling was held constant at full value.

The experimental data recorded included the following information.

Glyeeryl monostearate. b Mixture of 50% glyceryl monostearate and 50% stearyl lactyllc acid containing 0.9 lactyl groups per molecule.

EXAMPLE 7 Using the same method as described in Example 6 a monoand diglyceride preparation which contained 40% monoglyceride and 50% diglyceride was tested.

The pertinent data was as follows:

Glyceride containing monoglyceride and diglyceride. d Mixture of 50% and 50% stearyl lactylic acid containing 0.9 lactyl groups per molecule.

EXAMPLE 8 With the method outlined in Example 6, a propylene glycol monostearate preparation was evaluated.

The pertinent data was as follows:

Use Level Batter, Cake, Cake, Cake, 40 (Based on Emulsifier Specific Volume Specific Total Total Flour) Gravity (cc.) Volume Quality Score One part 0.892 760 2. 3 75. 5

One part 0.813 890 2. 7 78. 5

One part 0.743 800 2. 5 78.0

Two part 0.884 770 2. 3 82.5

Two part n..- 0.837 970 3. 0 85. 5

Two part L... 0. 989 1, 000 3. 0 85. 0

groups per molecule.

EXAMPLE 9 The testing method outlined in Example 6 was employed using a commercial glyceryl lactopalmitate preparation.

The pertinent data was as follows:

Use Level Batter, Cake, Cake, Cake, (Based on Emulstfier Specific Volume Specific Total Total Flour) Gravity (cc.) Volume Quality Score One part 0. 874 810 2. 4 73. 0

One part an--. 0. 884 1, 000 3. 0 85. 0

One part m 0. 870 995 3. 10 84. 5

One part 0. 870 900 2. 7 82. 5

TWO part L 0. 880 790 2. 4 81. 5

Two part L-.. O. 839 990 3. 0 86. 0

Two part 0.787 1, 080 3. 2 84. 5

Glyceryl lacto ahnitate. Mixture of 50 0 g and 50% stearyl laetylic acid containing 0.9 lactyl groups per molecule.

EXAMPLE 10 Example 6 was repeated, with the exception that a commercial preparation of the compound glyceryl lactostearate was evaluated.

The pertinent data was as follows:

Use Level Batter, Cake, Cake, Cake, (Based on Emulsifier Specific Volume Speclfic Total Total Flour) Gravity (cc.) Volume Quality Score 0.925 780 2. 35 74.0 One part i 0. 904 820 2. 71. 0 One part i 0.870 910 2. 8 82. 0 One part i 0. 864 960 2. 9 82. 5 One part i 0.890 900 2. 7 82.0 Two part 0.000 800 2.4 79.5 Two part 0. 860 1, 000 3.1 86. 5 Two part 0.781 1,030 3.1 84.0

f Glyceryl lactostearate. I Mixture of 50% i and 50% stearyl lactylic ac1d contaming 0.9 lactyl. groups per molecule.

EXAMPLE 1 1 Example 6 was again repeated using the compound sorbitan monostearate.

Sorbitan monostearate. 4 Mixture of 50% k and 50% stearyl lactylle acid contaunug 0.9 lactyl groups per molecule.

EXAMPLE 12 The compound polyoxyethylene (20) sorbitan monostearate was tested using the procedure detailed in Example 6.

The pertinent data was as follows:

Use Level Batter, Cake, Cake, Cake, (Based on Emulsifier Specific Volume Specific Total Total Flour) Gravity (cc.) Volume Quality Score One part 0.947 780 2. 3 63.5

Two part 0.815 820 2. 5 84.5

Two part 0.791 1, 050 3. 2 84. 5

m Polyoxyethylene (20) sorbitan monostearate. I Mixture of 50% m and 50% stcaryl lactylic acid containing 0.9 lactyl groups per molecule.

EXAMPLE 13 Example 6 was again repeated with a mixture of 90% sorbitan monostearate and polyoxyethylene sorbitan monostearate making up the base emulsifier.

The pertinent data was as follows:

Use Level Batter, Cake. Cake, Cake, (Based on Emulsifier Specific Volume Specific Total Total Flour) Gravity (00.) Volume Quality Score One part 0 0. 906 850 2. 6 78.0

One part 0.925 800 2. 7 77.5

One part 0.955 930 2. 8 78. 0

Two part n-.. 0.874 790 2. 4 82.5

Two part 0. 896 1, 020 3. 1 86. 5

Two part 0. 856 960 2. 0 81. 0

e A mixture of 90% sorbitan monostearate and 10% polyoxyethylene (20) sorbitan monostearate.

v A mixture of o and 50% stearyl lactyhc acid eontauung 0.9 lactyl groups per molecule.

The results of the tests shown in Examples 6 through 13 clearly demonstrate that the cakes produced with shortening modified with the two part addition agents of Examples 1 through 5 have lower batter specific gravity, higher quality score and increased cake volume than do cakes produced with shortening not modified according to the present invention.

EXAMPLE 14 To demonstrate in part the action of the agents of this invention, a typical cream filling formulation was employed. The ingredients and procedure were as follows:

for ten minutes at speed number 8 using a Hamilton Beech Model G mixer. The bowl was scraped down, the remainder of the water was added, and mixing continued for six additional minutes. Specific gravity and volume were measured together with liquid separation after hours. For comparative results, the following additives were substituted for part of the shortening in the above formula.

Variable #l8 grams of monoand diglyceride containing 40% monoand 50% diglyceride.

Variable #2-4 grams of the same monodiglyceride and 4 grams of a sodium salt of a stearyl lactylic acid preparation.

The results of this test are summarized in the following table.

Specific Volume Mls. Bleed, Variable Gravity (ml.) 140 Hours at 72 F.

These data exhibit the advantage derived by these improved emulsification agents. Increased volume and improved stability of the produced food product are in evidence.

EXAMPLE 15 The effects of the new addition agents of the present invention may the demonstrated in part 'by use in typical yellow cake formulation. An agent was formulated, including 35 parts palmityl lactylic acid which contained on the average 0.6 lactyl group per molecule, 30.5 parts distilled monoglyccride, 9 parts polyoxyethylene (20) sonbitan monostearate, and 20.5 hydrogenated vegetable oil. The homogeneous molten mixture was mixed with a small stirrer and rapidly chilled until the combination was a soft plastic not unlike typical cake shortening.

This preparation was compared with a product resultant from a similar preparation which did not include the palmityl lactylic acid. This agent is referred to as the base combination.

The following ingredients and procedure were employed in the test.

Ingredients Bakers Gms.

Percent Cake flour 100. 0 354. 7 3. 0 10. 6 0. 0 21. 3 120. 0 425. 7 12. 5 44. 3 0. 4 l. 4 40. 0 142. 0 50. 0 177. 4 110. 0 390. 0

The shortening and emulsifier were added to 858 gms. dry ingredients and mixed for four minutes at first speed using a Hobart C4 mixer equipped with a three quart bowl and batter paddle.

10 The dry ingredients, eggs, emulsifier and 218 m1. Otf water were placed in the bowl and mixed for one minute on first speed. The bowl was then scraped and the batter mixed for fiwe minutes on third speed. The bowl First stage.-Over a one minute period, 21 0 mls. of 5 was again scraped down and 150 ml. of water added over water was added while mixing on first speed, the bowl a one minute period while mixing on first speed. The was scraped and then mixed at first speed for two minbowl was scraped and mixing continued four minutes utes. longer.

Second stage.All of the eggs were added over a one 368 gms. of batter at a temperature of 72 F. were minute period at first speed, the bowl was scraped and placed in 8 inch round, greased cake pans and baked for mixing continued two and one-haltf minutes at second twenty-five minutes at 375 1F. speed.

Third stage-Over a one minute period, 180 mls. of Water was added while mixing at first speed, the bowl White batter whip cake was scraped down and mixing continued three minutes at first P Usin a c 100 Hob art mixer e u e h h The temperature of the water and eggs was controlled 1 q lpp d Wlt a t tee quart ow and awire whip. whereby the batter temperature was maintained between 70 and 7 3 F.

368 grams of batter was scaled into two 8 inch round In redient B k G cake pans and balked at 375 F. for twenty-five minutes. g s P3031 1: Wei g h ed Cakes were allowed to cool forty-five minutes prior to measuring volume by rape seed displacement and cutting 100.0 364.0 for quality comparison. 2-8 g-g Quality score was again determined as detailed in Ex- Salt 310 1019 ample 6. 2-8 fi' The data recorded included the following information: 0 12714 hole eggs 8.0 29. 1 Emnlsifipr 3. O 11. 5 Batter, Cake, Cake, 60. 0 218. 4 Use Level (Based on Total Specific Volume Specific 0.4 1.5 Flour) Gravity (00.) Volume 0. 4 1. 5 41.2 150.0

0.5% palmityl-0.6 laotylic acid plus basecombination. 0. 821 1, 000 3. 1 90. 0 0-5%basewmbmat10n 0-925 910 8 35 The dry ingredients, eggs, emulsifier and 218.4 cc. of

As the above data indicates, the inclusion of palmityl lactylic acid induced a substantial improvement in the yellow layer cake.

EXAIMPLE 16 Example '6 was repeated using the agents prepared as detailed in Example 15.

The following data was recorded.

Batter, Cake, Cake, Cake, Use Level (Based on Total Specific Volume Specific Total Flour) Gravity (cc.) Volume Quality Score 2% palrnity1-0.6 lactylic acid plus base combination 0.866 980 2. 9 93. 5 2% base combination 0.935 820 2. 5 83. 0

The results were similar to those found in Example 15.

EXAMPLE 17 Similar comparisons were made using a whip batter formulation which did not contain shortening.

Yellow batter whip cake Using a C-1.00 Hobart mixer equipped with a three quart bowl and wire whip.

water were placed in the bowl and mixed for two minutes on first speed. The bowl was scraped down and mixing continued for nine minutes on third speed.

The bowl Was again scraped and cc. of water was added over a one minute period on first speed, the bowl was scraped down again. The batter was mixed three minutes additional on first speed. 368.4 grams were baked in 8 inch pans at 370 F. for twenty-four minutes. The batter temperature was 72 F.

Data compiled are included in the tables. In the tables, the base combination is that of Example 15.

Yellow batter whip cake Batter, Cake, Cake, Cake, Use Level (Based on Total Specific Volume Specific Total Flour) Gravity (cc.) Volume Quality Score 3% arachidyl-2 lactylic acid lus combination 0. 785 1, 030 3. 2 91. 5 3% base combination 0. 853 920 2. 9 80. 5

White batter whip cake Batter, Cake, Cake, Cake, Use Level (Based on Total Specific Volume Specific Total Flour) Gravity (cc.) Volume Quality Score 3% stearyl-O.81acty1ic acid lus base combination.--" 0. 816 1, 010 3.0 90.0 3 0 base combination 0.980 875 2. 5 78.0

These results again clearly exhibit the desirable improvement afforded by the new emulsifier agents of the present invention.

I 1 EXAMPLE 1:;

Bread was prepared using the following formula and procedure:

A sixty-five percent sponge was used on the basis of 800 grams of flour for each dough. An absorption of sixty-four percent of the weight of flour was added for sponging. The yeast was emulsified in part of the sponge water prior to the addition to the flour. The total yeast food was added to the sponge.

The sponge was mixed one-half minute at low speed in a Hobart A-120 mixer, then four minutes in second speed. The sponge was placed in a metal trough and fermented at 80 F. for four and one-half hours.

Dough was mixed as follows: the fermented sponge, the balance of the dry ingredients and the remaining water were placed in the mixing bowl. Mixing was initiated at low speed for one-half minute and then second speed for seven and one-half minutes. The dough temperature was regulated to 80 F.

Immediately after mixing, the dough was placed in the fermentation cabinet for forty minutes. At the end of that period, the dough was removed and two 542 gram pieces scaled. Each was processed through a dough sheeter and allowed to stand at room temperature for ten minutes.

Each piece was then moulded in a conventional commercial moulder, placed in a pan and proofed at 110 F. dry bulb and 105 F. wet bulb until the surface of the double was /1 inch above the top of the pan.

The doughs were then baked at 415 F. for twentyfive minutes.

Following baking, the loaves were removed from the oven, placed on a rack and cooled for seventy minutes and finally placed in polyethylene bags for twelve hours prior to scoring.

Following scoring, the compressibility of two inch sections of the bread crumb was measured using a Labline compressometer equipped with a three centimeter diameter cylinder (260 gins.) and graduated in tenths of a millimeter. The penetrations of a fresh cut section in ten seconds was measured and recorded. This procedure was repeated with four duplicate samples to provide an average value. Sample loaves were stored at 78 F. in air tight containers, compressibility measured after three and five days storage.

The following results were obtained:

As can be seen from the data, the addition of the agent of the present invention resulted in improvement in apparent stalling and quality.

The invention in its broader aspects is not limited to the specific compositions, steps and methods described, but departures may be made therefrom within the scope '12 of the accompanying claims without departing from the principles of the invention and without sacrificing its chief advantages.

What is claimed:

1. An emulsification addition agent which comprises, in combination: (1) a composition comprising an acyl lactylic acid compound corresponding to the formula wherein RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtues thereof, n is greater than zero and less than 1, and Z is a member selected from the group consisting of hydrogen and alkali metal; and (2) a composition comprising a member selected from the group consisting of mono-fatty acid esters, di-fatty esters, and mixtures of monoand di-fatty acid esters of aliphatic polyhydric alcohol compounds the acyl component of said esters having about 16 to 24 carbon atoms; the weight ratio of composition (1) to composition (2) being between about 0.01 and 100.

2. An emulsification agent for bakery goods which comprises, in combination: (1) a composition comprising an acyl lactylic acid compound corresponding to the formula RCO(OCHCH CO) OZ wherein RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtures thereof, It is greater than zero and less than 1 and Z is a member selected from the group consisting of hydrogen and alkali metal; and (2) a composition comprising a member selected from the group consisting of mono-fatty acid esters, di-fatty esters, and mixtures of monoand di-fatty acid esters of aliphatic polyhydric alcohol compounds the acyl component of said esters having about 16 to 24 carbon atoms and the alcohol component having less than about 12 carbon atoms; the weight ratio of composition (1) to composition (2) being between about 0.01 and 100.

3. The agent of claim 2 wherein the said weight ratio is between about 0.33 and 10.

4. An addition agent for bakery goods which comprises, in combination: 10 to weight percent of a composition comprising an acyl lactylic acid compound corresponding to the formula wherein RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtures thereof, n is about 0.3 to 0.9 and Z is a member selected from the group consisting of hydrogen and alkali metal; and 90 to 10 weight percent of a composition comprising mono-fatty acid esters of glycerol the acyl component of said esters having about 16 to 24 carbon atoms.

5. The addition agent of claim 4 wherein the composition comprising mono-fatty acid esters of glycerol includes di-fatty acid esters of glycerol.

6. An addition agent for bakery products which comprises, in combination: 1 to 99 weight percent of a composition comprising an acyl lactylic acid compound corresponding to the formula RCO (OCHCH C0) OZ wherein RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtures thereof, it is about 0.3 to 0.9 and Z is a member selected from the group consisting of hydrogen and alkali metal; and 99 to 1 weight percent of a composition comprising 5 to 20 weight percent polyoxyethylene sorbitan mono-stearate and 80 to weight percent sorbitan monostearate.

7. An addition agent for bakery products which comprises, in combination: 1 to 99 weight percent of a composition comprising: an acyl lactylic acid compound corresponding to the formula RCO(OCHCH CO),,OZ

RCO (OCHCH CO) ,OZ

wherein RC is a member selected from the group consisting of acyl radicals of fatty acids containing 1 6 to 24 carbon atoms, and mixtures thereof, n is about 0.3 to 0.9 and Z is a member selected from the group consisting of hydrogen and alkali metal; and 99 to 1 weight percent of a composition comprising sorbitan monostearate.

9. An addition agent for bakery products which comprises, in combination: 10 to 90 weight percent of a composition comprising: an acyl lactylic acid compound corresponding to the formula RCO (OCHCH CO) OZ wherein RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtures thereof, n is about 0.3 to 0.9 and Z is a member selected from the group consisting of hydrogen and alkali metal; and 90 to 10 weight percent of a composition comprising propylene glycol monostearate.

10. An addition agent for bakery products which comprises, in combination, 10 to 90 weight percent of a composition comprising: an acyl lactylic acid compound cor responding to the formula RCO(OCHCH CO) OZ wherein RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtures thereof, n is about 0.3 to 0.9

and Z is a member selected from the group consisting of hydrogen and alkali metal; and to 10 weight percent of a composition comprising glyceryl lactopalmitate.

11. An addition agent for bakery products which comprises, in combination, -10 to 90 weight percent composi- 14 tion comprising: an acyl lactylic acid compound corresponding to the formula RCO (OCHCH CO OZ wheerin RC0 is a member selected from the group consisting of acyl radicals of fatty acids containing 16 to 24 carbon atoms, and mixtures therof, n is about 0.3 to 0.9 and Z is a member selected from the group consisting of hydrogen and alkali metal; and 90 to 10 weight percent of a composition comprising glyceryl lactostearate.

12. The emulsification addition agent of claim 1 wherein said addition agent includes water as a component and wherein the value of n for the acyl lactylic acid compound is about 0.3 to 0.9.

13. The emulsifica-tion addition agent of claim 1 wherein the value of n for the acyl lactylic acid compound is, on the average, 0.3 to 0.9, and the Z of the acyl lactylic acid compound is a member selected from the group consisting of sodium and potassium.

14. The method of claim 1 wherein the value of n for the acyl lactylic acid compound is, on the average, 0.3 to 0.9, and the Z of the acyl lactylic acid compound is hydrogen.

References Cited by the Examiner UNITED STATES PATENTS 2,381,936 8/1945 Tiede 252-356 2,5 3 1,190 11/1950 Ackelsberg 252-356 2,690,971 10/ 1954 Iveson et a1 99-118 2,733,252 1/1956 Thompson et al 99-91 X 2,744,826 5/ 1956 Thompson et al. 99-91 2,886,438 5/1959 Barsky et al. 99-92 2,932,574 4/1960 Bour 99-91 2,963,371 12/1960 Young et al 99-118 3,033,686 5/1962 Landfried et al 99-91 3,141,030 7/1964 Buddemeyer et al. 99-91 X 3,180,736 4/ 1965 Landfried 99-91 FOREIGN PATENTS 561,704 8/ 1958 Canada.

OTHER REFERENCES The Journal of the American Oil Chemists Society," January 1958, vol. XXXV, No. 1, pp. 49-52.

A. LOUIS MONACELL, Primary Examiner.

ABRAHAM H. WINKELSTEIN, Examiner.

I. M. GOLIAN, R. N. JONES, Assistant Examiners.

UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,244,534 April 5, 1966 Bruce D. Buddemeyer et al.

It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Column 14, line 20, for "The method" read The emulsification addition agent Signed and sealed this 21st day of February 1967.

(SEAL) Attest:

ERNESFWCSWHDER EDVUHHIJ.BRENNER Attesting Officer Commissioner of Patents 

1. A EMULSIFICATION ADDITION AGENT WHICH COMPRISES, IN COMBINATION: (1) A COMPOSITION COMPRISING AN ACYL LACTYLIC ACID COMPOUND CORRESPONDING TO THE FORMULA 